We usually travel to Whitby on the Friday to be there bright and early and not miss any of the festival. I haven't yet booked B&B for that night (we have a flat for the week), and I suspect it might be difficult in Whitby itself - with the Regatta and all.
Are there any good sessions or sings planned in or near Whitby on Friday evening. E.g. if there was something on in Robin Hood's Bay we could try for accomodation there.